Total synthesis of (+)-calyculin A and (-)-calyculin B: Asymmetric synthesis of the C(9-25) spiroketal dipropionate subunit

Journal of the American Chemical Society

Volumn 121, Issue 45, 1999, Pages 10468-10477

  Smith III, Amos B ^a   Friestad, Gregory K ^a   Barbosa, Joseph ^a   Bertounesque, Emmanuel ^a   Hull, Kenneth G ^a   Iwashima, Makoto ^a   Qiu, Yuping ^a   Salvatore, Brian A ^a   Spoors, P Grant ^a   Duan, James J W ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CALYCULIN A; CALYCULIN B; MARINE TOXIN; PROPIONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHELATION; CYCLIZATION; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033579137     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992134m     Document Type: Article

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105. Coupling experiments with the TBS-piotected analogue of 57 were likewise unsuccessful.
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118. (a) For an application to synthesis of pseudomonic acid C, see: Balog, A.; Yu, M. S.; Curran, D. P.; Yu, G.; Carcanague, D. R.; Shue, Y.-K. Synth. Commun. 1996, 26, 935. (b) For an application to synthesis of swinholides, see: Paterson, I.; Cumming, J. G.; Smith, J. D.; Ward, R. A.; Yeung, K.-S. Tetrahedron Lett. 1994, 35, 3405, (c) For other recent synthetic applications, see: Pellissier, H.; Michellys, P.-Y.; Santelli, M. Tetrahedron Lett. 1994, 35, 6481; Money, T.; Wong, M. K. C. Tetrahedron 1996, 52, 6307.
119. (a) For an application to synthesis of pseudomonic acid C, see: Balog, A.; Yu, M. S.; Curran, D. P.; Yu, G.; Carcanague, D. R.; Shue, Y.-K. Synth. Commun. 1996, 26, 935. (b) For an application to synthesis of swinholides, see: Paterson, I.; Cumming, J. G.; Smith, J. D.; Ward, R. A.; Yeung, K.-S. Tetrahedron Lett. 1994, 35, 3405, (c) For other recent synthetic applications, see: Pellissier, H.; Michellys, P.-Y.; Santelli, M. Tetrahedron Lett. 1994, 35, 6481; Money, T.; Wong, M. K. C. Tetrahedron 1996, 52, 6307.
120. (a) For an application to synthesis of pseudomonic acid C, see: Balog, A.; Yu, M. S.; Curran, D. P.; Yu, G.; Carcanague, D. R.; Shue, Y.-K. Synth. Commun. 1996, 26, 935. (b) For an application to synthesis of swinholides, see: Paterson, I.; Cumming, J. G.; Smith, J. D.; Ward, R. A.; Yeung, K.-S. Tetrahedron Lett. 1994, 35, 3405, (c) For other recent synthetic applications, see: Pellissier, H.; Michellys, P.-Y.; Santelli, M. Tetrahedron Lett. 1994, 35, 6481; Money, T.; Wong, M. K. C. Tetrahedron 1996, 52, 6307.
121. (a) For an application to synthesis of pseudomonic acid C, see: Balog, A.; Yu, M. S.; Curran, D. P.; Yu, G.; Carcanague, D. R.; Shue, Y.-K. Synth. Commun. 1996, 26, 935. (b) For an application to synthesis of swinholides, see: Paterson, I.; Cumming, J. G.; Smith, J. D.; Ward, R. A.; Yeung, K.-S. Tetrahedron Lett. 1994, 35, 3405, (c) For other recent synthetic applications, see: Pellissier, H.; Michellys, P.-Y.; Santelli, M. Tetrahedron Lett. 1994, 35, 6481; Money, T.; Wong, M. K. C. Tetrahedron 1996, 52, 6307.
122. 1H NMR properties consistent with hemiketal i. ( Formula Presented)
123. Cupric acetate has been employed in industrial Wacker oxidations, see: Hrusovsky, M.; Vojtko, J.; Cihova, M. Hung. J. Ind. Chem. 1974, 2, 137; Chemical Abstracts 1975, 82, 139205.
124. Cupric acetate has been employed in industrial Wacker oxidations, see: Hrusovsky, M.; Vojtko, J.; Cihova, M. Hung. J. Ind. Chem. 1974, 2, 137; Chemical Abstracts 1975, 82, 139205.
125. 2 leads to chlorinated byproducts, see ref 66.
126. Piers, E.; Tillyer, R. D. J. Org. Chem. 1988, 53, 5366.
127. 2O, persisting for at least 2 days at -5 °C.
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129. Solladié reported the anti reduction of β-arylsulfinyl ketones with DIBAL, see: Solladié, G.; Detnailly, G.; Greek, C. Tetrahedron Lett. 1985, 26, 435. Although Solladié proposed an alternative mechanism, internal delivery of hydride has been proposed to explain these results; see: Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
130. Acetonide migration product (+)-76 and the product of desilylation of triol (+)-75 (isolated from larger scale deprotection experiments) could each be readily redirected to the synthetic sequence.
131. (a) Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945.
132. (b) Evans, D. A.; Rieger, D. L.; Gage, J. R. Tetrahedron Lett. 1990, 31, 7099.